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Polymeric compound containing metal complex residue and element comprising same

A technology of polymer compounds and metal complexes, which is applied in the fields of electrical components, organic chemistry, chemical instruments and methods, etc., and can solve the problems of not being able to obtain components with luminous efficiency

Inactive Publication Date: 2011-05-18
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, when the above-mentioned polymer compound is used in the manufacture of electroluminescent devices, etc., it is not possible to obtain devices with excellent luminous efficiency.

Method used

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  • Polymeric compound containing metal complex residue and element comprising same
  • Polymeric compound containing metal complex residue and element comprising same
  • Polymeric compound containing metal complex residue and element comprising same

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0312] (Synthesis of Metal Complex (MC-5))

[0313] [synthetic method 1]

[0314] ·Synthesis of 5-bromo-2-phenylpyridine

[0315] In a reaction vessel, measure 2,5-dibromopyridine (7.11 g, 30 mmol), toluene (130 mL), phenylboronic acid (4.57 g, 37.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.73 g , 1.5 mmol), under nitrogen flow, dissolve the reactants while stirring at 50°C. A 2M aqueous sodium carbonate solution (30 mL) was added thereto, followed by stirring at 80°C for 6 hours. The organic layer of the obtained reaction solution was recovered, and washed with an aqueous sodium carbonate solution and saturated brine. The organic layer was dried over sodium sulfate, filtered, and distilled off. The residue was purified by silica gel column chromatography (hexane / toluene), and the solvent was distilled off to obtain 5-bromo-2-phenylpyridine (6.21 g, 26.5 mmol).

[0316] Synthesis of metal complexes (complex 1 and 2)

[0317]

[0318] In a reaction vessel, m...

Embodiment 1

[0349] (Synthesis and evaluation of polymer compound 1)

[0350] Synthesis of metal complexes (MC-6, and MC-7)

[0351]

[0352] Under an argon flow, the metal complex (MC-5, 2.03 g, 1.20 mmol) and dichloromethane (200 mL) obtained in Synthesis Example 1 were weighed in a reaction container to dissolve the metal complex. N-bromosuccinimide (221 mg, 1.24 mmol) was added thereto, and stirred at room temperature for 4 hours. The solvent was distilled off, and toluene (50 mL) was added to the residue to dissolve it. This toluene solution was purified by silica gel chromatography (developing solvent: toluene). The eluted solution was recovered, and the solvent was distilled off, and a hexane / toluene (2 / 1) mixed solution (400 mL) was added to the residue to dissolve it. This solution was purified again by silica gel chromatography (developing solvent: hexane / toluene=2 / 1). The second eluted component was recovered, and the residue was washed with methanol after distilling off...

Embodiment 2

[0368] (synthesis and evaluation of polymer compound 2)

[0369] Under an inert atmosphere, 2,7-bis(1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (0.53g), 2,7-dibromo-9 , 9-dioctylfluorene (0.16g), 2,7-dibromo-9,9-dihexylfluorene (0.20g), bis(4-bromophenyl)-(4-sec-butylphenyl)- Amine (0.092g), metal complex (MC-7) (0.18g), Aliquat336 (0.13g, manufactured by Aldrich), bis(triphenylphosphine)palladium dichloride (0.7mg), and toluene (26ml) were mixed , heated to 105°C. 2M Na was added dropwise to the reaction solution 2 CO 3 Aqueous solution (10ml), refluxed for 4 hours. After the reaction, phenylboronic acid (0.12 g) was added, followed by heating at 105° C. for 5 hours. After cooling, it was washed three times with 3% by weight aqueous acetic acid (20 ml) and three times with water (20 ml), and purified by passing through an alumina column and a silica gel column. The obtained toluene solution was added dropwise to methanol (200 ml), and after stirring for 1 hour, the re...

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Abstract

A polymeric compound contains a residue of a metal complex represented by formula (1), wherein M represents a metal atom selected from ruthenium, rhodium, palladium, osmium, iridium and platinum; R1, R2, R3, R4, R5, R6 and R8 independently represent a hydrogen atom, a halogen atom, an alkyl group, or the like; m represents an integer of 1 to 3; n represents an integer of 0 to 2; Z1, Z2, Z3, Z4 and Z5 independently represent a carbon atom or a nitrogen atom, provided that at least two member of Z1, Z2, Z3, Z4 and Z5 represent a nitrogen atom, and when any one member of Z1, Z2, Z3, Z4 and Z5 represents a carbon atom, a hydrogen atom bound to the carbon atom may be substituted by a substituent; a moiety represented by formula (2) represents a bidentate monoanionic ligand; and Rx and Ry are atoms bound to the metal atom M and independently represent a carbon atom, an oxygen atom or a nitrogen atom, and a bivalent group.

Description

technical field [0001] The present invention relates to a polymer compound containing a residue of a metal complex and an element containing the same. Background technique [0002] Various metal complexes can be used as the light-emitting material used in the light-emitting layer of the electroluminescence element. In addition, a light-emitting material using the structure of the metal complex as a repeating unit of a polymer has also been proposed. For example, an ortho-metallated complex with iridium as the central metal (Ir(ppy) 3 : A polymer compound having a structure of a tri(ortho-metallated) iridium (III) complex) of 2-phenylpyridine and a fluorenediyl group as a repeating unit in a ligand (Patent Document 1). [0003] Patent Document 1: Japanese Unexamined Patent Publication No. 2003-73479 [0004] However, when the above-mentioned polymer compound is used to manufacture an electroluminescent device or the like, a device with excellent luminous efficiency cannot ...

Claims

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Application Information

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IPC IPC(8): C08G61/00C07D401/04C07D401/14C08L65/00C09K11/06H01L51/50
CPCC08G2261/411C08G61/122C09K2211/185C09K2211/1416H05B33/14C09K2211/1466C07D401/04C07D401/14H01L51/0043C08G2261/149H01L51/0036H01L51/0039H01L51/0085C09K2211/1425C08G2261/1526C08G2261/3162C08G61/12H01L51/5016C09K11/06C08G2261/3142H10K85/115H10K85/151H10K85/113H10K85/342H10K50/11H10K2101/10
Inventor 秋野喜彦冈村玲
Owner SUMITOMO CHEM CO LTD
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